US7285560B2 - Indole derivatives or benzimidazole derivatives for modulating IκB kinase - Google Patents

Indole derivatives or benzimidazole derivatives for modulating IκB kinase Download PDF

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US7285560B2
US7285560B2 US10/642,970 US64297003A US7285560B2 US 7285560 B2 US7285560 B2 US 7285560B2 US 64297003 A US64297003 A US 64297003A US 7285560 B2 US7285560 B2 US 7285560B2
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alkyl
hydrogen
indole
methylaminopyrimidin
ethyl
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US20050197353A1 (en
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Olaf Ritzeler
Gerhard Jaehne
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Sanofi Aventis Deutschland GmbH
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Definitions

  • the invention relates to indole derivatives or benzimidazole derivatives which inhibit I ⁇ B kinase, to processes for preparing them and to their use as pharmaceuticals.
  • the first step in the abovementioned signal cascade is the breakdown of I ⁇ B. This phosphorylation is regulated by the specific I ⁇ B kinase. Thus far, no inhibitors are known which inhibit I ⁇ B kinase specifically.
  • the invention furthermore relates to compounds of the formula I, where
  • “Pharmaceutically effective amount” is meant to describe an amount of a compound, composition, medicament or other active ingredient effective in producing the desired therapeutic effect.
  • the invention also relates to a process for producing a pharmaceutical which comprises bringing at least one compound of the formula I together with a pharmaceutically suitable and physiologically tolerated excipient and, where appropriate, other suitable active compounds, additives or auxiliary substances, into a suitable form for administration.
  • Empirical formula C 11 H 9 N 2 ; M.W. 188.21; MS (M+H) 189.1.
  • Empirical formula C 25 H 32 FN 3 O 6 ; M.W. 489.55; MS (M+H) 490.6.
  • the plasma samples were thawed.
  • the plasma proteins which interfered with the analysis were then precipitated with acetonitrile.
  • the lower detection limit of the method is 0.01 ⁇ g/mL.
  • the lower detection limit was identical to that when employing LC-MS/MS in the example using the compound 28.

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US10/642,970 2002-08-17 2003-08-18 Indole derivatives or benzimidazole derivatives for modulating IκB kinase Expired - Lifetime US7285560B2 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
US10/642,970 US7285560B2 (en) 2002-08-17 2003-08-18 Indole derivatives or benzimidazole derivatives for modulating IκB kinase
US11/758,978 US8778955B2 (en) 2002-08-17 2007-06-06 Indole derivatives or benzimidazole derivatives for modulating IkB kinase

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
DE10237722A DE10237722A1 (de) 2002-08-17 2002-08-17 Indol- oder Benzimidazolderivate zur Modulation der IKappaB-Kinase
DE10237722.7 2002-08-17
US43474902P 2002-12-19 2002-12-19
US10/642,970 US7285560B2 (en) 2002-08-17 2003-08-18 Indole derivatives or benzimidazole derivatives for modulating IκB kinase

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US7285560B2 true US7285560B2 (en) 2007-10-23

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EP (2) EP2233483B1 (de)
JP (1) JP4504812B2 (de)
KR (1) KR101162046B1 (de)
CN (1) CN1314683C (de)
AR (1) AR040975A1 (de)
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AU (1) AU2003263196B2 (de)
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CA (1) CA2498559C (de)
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DE (2) DE10237722A1 (de)
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Cited By (8)

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US20070142417A1 (en) * 2005-05-11 2007-06-21 Aventis Pharmaceuticals Inc Substantially Pure 2-{[2-(2-Methylamino-Pyrimidin-4-YL)-1H-Indole-5-Carbonyl]-Amino}-3-Phenylpyridin-2-YL-Amino)-Propionic Acid as an IkB Kinase Inhibitor
US20070244139A1 (en) * 2002-08-17 2007-10-18 Sanofi-Aventis Deutschland Gmbh Indole Derivatives or Benzimidazole Derivatives for Modulating IkB Kinase
US20080214813A1 (en) * 2005-06-01 2008-09-04 Sanofi-Aventis Method for producing 2-(2-aminopyrimidin-4-yl)-1h-indole-5-carboxylic acid derivatives
US20090203918A1 (en) * 2004-07-10 2009-08-13 Sanofi-Aventis Deutschland Gmbh Method for producing enantiomeric form of 2,3-diaminopropionic acid derivatives
WO2013083553A1 (en) 2011-12-06 2013-06-13 Sanofi Crystalline forms of 2-(2-methylamino-pyrimidin-4-yl)-1h-indole-5-carboxylic acid [(s)-1-carbamoyl-2-(phenyl-pyrimidin-2-yl-amino)-ethyl]-amide
US8877926B2 (en) 2010-08-12 2014-11-04 Sanofi Process for the preparation of enantiomeric forms of 2,3-diaminopropionic acid derivatives
EP2805705A1 (de) 2013-05-23 2014-11-26 IP Gesellschaft für Management mbH Verpackung enthaltend Verabreichungseinheiten von Natriumsalzen der (R)-3-[6-amino-pyridin-3-yl]-2-(1-cyclohexyl-1 H-imidazol-4-yl)-Propionsäure
US9968605B2 (en) 2014-07-03 2018-05-15 Sanofi 2-(2-methylamino-pyrimidin-4-yl)-1h-indole-5-carboxylic acid [(S)-1-carbamoyl-2-(phenyl-pyrimidin-2-yl-amino)-ethyl]-amide for use in the treatment of pain associated to osteoarthritis

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DE10237723A1 (de) * 2002-08-17 2004-07-08 Aventis Pharma Deutschland Gmbh Verwendung von IKappaB-Kinase Inhibitoren in der Schmerztherapie
US8293751B2 (en) 2003-01-14 2012-10-23 Arena Pharmaceuticals, Inc. 1,2,3-trisubstituted aryl and heteroaryl derivatives as modulators of metabolism and the prophylaxis and treatment of disorders related thereto such as diabetes and hyperglycemia
AR045047A1 (es) * 2003-07-11 2005-10-12 Arena Pharm Inc Derivados arilo y heteroarilo trisustituidos como moduladores del metabolismo y de la profilaxis y tratamiento de desordenes relacionados con los mismos
AR049274A1 (es) * 2004-05-12 2006-07-12 Aventis Pharma Inc Acido2-{[2-(2-metilaminopirimidin-4-il)-1h-indol-5-carbonil]amino}-3-(fenilpiridin-2-ilamino)propionico sustancialmente puro como inhibidor selectivo de la quinasa ikk-2
PE20060373A1 (es) 2004-06-24 2006-04-29 Smithkline Beecham Corp Derivados 3-piperidinil-7-carboxamida-indazol como inhibidores de la actividad cinasa de ikk2
PE20060748A1 (es) 2004-09-21 2006-10-01 Smithkline Beecham Corp Derivados de indolcarboxamida como inhibidores de quinasa ikk2
DOP2006000010A (es) * 2005-01-10 2006-07-31 Arena Pharm Inc Procedimiento para preparar eteres aromáticos
AR053114A1 (es) * 2005-01-12 2007-04-25 Aventis Pharma Inc Sal monopotasica del acido 2-{[2-(-2-metilamino-pirimidin-4-il)-1h-indol-5-carbonil]-amino}-3-(fenilpiridin-2-il-amino)-propionico,inhibidora de ikk-2 quinasa
PE20070173A1 (es) 2005-06-30 2007-03-14 Smithkline Beecham Corp Compuestos de indol carboxamidas como inhibidores de ikk2
US8063071B2 (en) 2007-10-31 2011-11-22 GlaxoSmithKline, LLC Chemical compounds
US8093401B2 (en) * 2005-08-04 2012-01-10 Sirtris Pharmaceuticals, Inc. Sirtuin modulating compounds
WO2007019345A1 (en) * 2005-08-04 2007-02-15 Sirtris Pharmaceuticals, Inc. Imidazopyridine derivatives as sirtuin modulating agents
US8088928B2 (en) * 2005-08-04 2012-01-03 Sirtris Pharmaceuticals, Inc. Sirtuin modulating compounds
US7855289B2 (en) * 2005-08-04 2010-12-21 Sirtris Pharmaceuticals, Inc. Sirtuin modulating compounds
EA200800755A1 (ru) 2005-09-07 2008-10-30 Лаборатуар Сероно С.А. Ikk ингибиторы, предназначенные для лечения эндометриоза
JP2009001495A (ja) * 2005-10-13 2009-01-08 Taisho Pharmaceutical Co Ltd ２−アリール−ベンゾイミダゾール−５−カルボキサミド誘導体
BRPI0715160A2 (pt) 2006-08-08 2013-06-11 Sanofi Aventis imidazolidina-2,4-dionas substituÍdas por arilamimoaril-alquil-, processo para preparÁ-las, medicamentos compeendendo estes compostos, e seu uso
AR065804A1 (es) 2007-03-23 2009-07-01 Smithkline Beecham Corp Compuesto de indol carboxamida, composicion farmaceutica que lo comprende y uso de dicho compuesto para preparar un medicamento
TW200916472A (en) * 2007-06-20 2009-04-16 Sirtris Pharmaceuticals Inc Sirtuin modulating compounds
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